CN113549087A - Compound and application thereof - Google Patents
Compound and application thereof Download PDFInfo
- Publication number
- CN113549087A CN113549087A CN202010338424.4A CN202010338424A CN113549087A CN 113549087 A CN113549087 A CN 113549087A CN 202010338424 A CN202010338424 A CN 202010338424A CN 113549087 A CN113549087 A CN 113549087A
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- Prior art keywords
- compound
- substituted
- unsubstituted
- heteroaryl
- aryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 141
- 239000000463 material Substances 0.000 claims abstract description 40
- 230000002950 deficient Effects 0.000 claims abstract description 11
- 239000010410 layer Substances 0.000 claims description 99
- -1 cyano, carbonyl Chemical group 0.000 claims description 50
- 230000005525 hole transport Effects 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000002346 layers by function Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 2
- 230000004927 fusion Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 238000002347 injection Methods 0.000 abstract description 25
- 239000007924 injection Substances 0.000 abstract description 25
- 238000013508 migration Methods 0.000 abstract description 5
- 230000005012 migration Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 230000021615 conjugation Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 31
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000004440 column chromatography Methods 0.000 description 20
- 238000001704 evaporation Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 11
- 239000010408 film Substances 0.000 description 9
- 239000011368 organic material Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 7
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000008204 material by function Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- RXELBMYKBFKHSM-UHFFFAOYSA-N 2-phenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC=NC=N1 RXELBMYKBFKHSM-UHFFFAOYSA-N 0.000 description 2
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 1
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 1
- ONCCVJKFWKAZAE-UHFFFAOYSA-N 2-bromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=C(Br)C=C12 ONCCVJKFWKAZAE-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- IRAOSCSPAYZRJE-UHFFFAOYSA-N 5-bromoquinoxalin-6-amine Chemical class N1=CC=NC2=C(Br)C(N)=CC=C21 IRAOSCSPAYZRJE-UHFFFAOYSA-N 0.000 description 1
- SYACRXBYRNYMLN-UHFFFAOYSA-N 9-bromo-10-naphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 SYACRXBYRNYMLN-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 101000930898 Cryphonectria parasitica Glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- XEFCWBLINXJUIV-UHFFFAOYSA-N acetic acid;iodobenzene Chemical compound CC(O)=O.CC(O)=O.IC1=CC=CC=C1 XEFCWBLINXJUIV-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H10K50/16—Electron transporting layers
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
Abstract
The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula (1), the compound has a structure in which an Ar group is connected with a 5, 6-oxazoloquinoxaline electron-deficient large conjugated structure as a parent nucleus, the compound structure has stronger electron-deficient property and is favorable for electron injection, and meanwhile, the electron-deficient group of the large conjugated structure enables molecules to have good plane conjugation, so that the mobility of electrons is improved, and the molecules integrally show good electron injection and migration performances, therefore, when the compound is used, the compound has the structure shown in the formula (1)When the compound is used as an organic electroluminescent device, particularly as an electron transport layer material, the electron injection and migration efficiency in the device can be effectively improved, so that the excellent effects of high luminous efficiency and low starting voltage of the device are ensured.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
Organic Light Emission Diodes (OLED) devices are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. This is because an efficient, long-lived OLED device is generally the result of an optimized configuration of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.
In order to prepare an OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device need to be innovated, and photoelectric functional materials in the OLED device need to be continuously researched and innovated, so that functional materials with higher performance can be prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
In order to further satisfy the continuously increasing demand for the photoelectric properties of OLED devices and the energy saving demand of mobile electronic devices, new and efficient OLED materials need to be continuously developed, wherein the development of new electron transport materials with high electron injection capability and high mobility is of great significance.
Disclosure of Invention
The object of the present invention is to provide a compound having a higher electron injection ability and a higher electron mobility.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound, which has a structure shown in a formula (1);
in the formula (1), X is S or O;
in formula (1), the R represents one substituent to the maximum permissible substituent, and is independently selected from hydrogen, deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, and when the number of R is multiple, adjacent R can be connected in a condensed mode;
in the formula (1), L is selected from one of single bond, substituted or unsubstituted arylene of C6-C60 and substituted or unsubstituted heteroarylene of C3-C60; l is preferably one of a single bond, a substituted or unsubstituted arylene group with C6-C30, and a substituted or unsubstituted heteroarylene group with C3-C30;
in the formula (1), Ar is selected from one of substituted or unsubstituted aryl of C6-C60 and substituted or unsubstituted heteroaryl of C3-C60; ar is preferably one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
Further, the compounds of the present invention have the structures represented by the following formulae (1-1) to (1-3):
in the formulae (1-1) to (1-3), the X, R, Ar and L are defined as in the formula (1).
Still further, the compound of the present invention has any one of the following structures represented by formulae (a) to (j):
in the formulae (a) to (j), R1-R4The same or different, and each is independently selected from one of hydrogen, deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, and R is1-R4Wherein two adjacent groups may be connected by fusion;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30. Further preferably, in formula (1), formula (1-1) to formula (1-3), formula (a) to formula (j) of the present invention, Ar is selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, cyano; more preferably, Ar is selected from substituted or unsubstituted C3-C30 electron deficient heteroaryl or cyano.
The "electron-deficient heteroaryl group (may be referred to as an electron-deficient group)" in the present specification means a group in which the electron cloud density on the benzene ring is decreased after the group substitutes for hydrogen on the benzene ring, and usually such a group has a Hammett value of more than 0.6. The Hammett value is a representation of the charge affinity for a particular group and is a measure of the electron withdrawing group (positive Hammett value) or electron donating group (negative Hammett value). The Hammett equation is described In more detail In Thomas H.Lowry and Kathelen Schueler Richardson, "mechanics and Theory In Organic Chemistry", New York,1987, 143-. Such groups may be listed but are not limited to: triazinyl, pyrimidinyl, benzopyrimidinyl, benzopyridyl, naphthyridinyl, phenanthridinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, pyridazinyl, and alkyl-or aryl-substituted ones of the foregoing.
More preferably, in formula (1), formula (1-1) to formula (1-3), and formula (a) to formula (j), Ar is selected from a cyano group or any one of the following substituted or unsubstituted groups:
wherein, the wavy line
Indicates the attachment site.
When the structural formula is substituted, the substituted group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
Still more preferably, R, R described above1-R4Each independently selected from hydrogen, deuteriumOr the following substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, perylenyl, anthrylenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenylenyl, trimeric indenyl, isotridecylinyl, trimeric spiroindenyl, spiromesityl, spiroisotridecylinyl, furanyl, isobenzofuranyl, phenyl, terphenyl, anthryl, terphenyl, pyrenyl, terphenyl, etc., p-o, etc Dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, pyrimidyl, benzopyrimidinyl, quinoxalyl, 1, 5-diazaanthracenyl, 2, 7-diazenylene group, 2, 3-diazenylene group, 1, 6-diazenylene group, 1, 8-diazenylene group, 4,5,9, 10-tetraazaperyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinylOne of benzothiadiazolyl, or a combination of two of the foregoing.
Furthermore, the compounds described by the general formula of the present invention may preferably be compounds of the following specific structures represented by C1-C91, which are merely representative:
the second object of the present invention is to provide the use of the compound according to the first object for the application in organic electronic devices.
Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner, or electronic paper, preferably an organic electroluminescent device.
Preferably, the compound is used as an electron transport material in the organic electroluminescent device.
The compound of the present invention has high electron affinity, so that the compound has strong electron accepting capacity and is suitable for use as electron transporting material, but is not limited to this.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layer contains the compound of the general formula of the present invention represented by any one of the above general formulae or contains the compound represented by each of the above specific formulae.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
Specifically, one embodiment of the present invention provides an organic electroluminescent device including a substrate, and an anode layer, a plurality of light emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; wherein the electron transport layer contains the compound of the general formula of the present invention represented by the above formula (1).
More specifically, the organic electroluminescent device will be described in detail.
The OLED device includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be used as the first electrode by sputtering or deposition on the substrateThe manner of the material. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multi-layer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), and aromatic amine derivatives as shown below in HT-1 to HT-51; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; one or more of the compounds HT-1 to HT-51 may also be used to dope one or more of the compounds HI-1 to HI-3 described below.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, the combination of one or more of BFD-1 through BFD-24 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light-emitting layer is selected from, but not limited to, one or more of PH-1 to PH-85.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.
Wherein D is deuterium.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of YPD-1 to YPD-11 listed below.
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described above; mixtures of one or more compounds from HT-1 to HT-51 and one or more compounds from PH-47 to PH-77 may also be used, but are not limited thereto.
The organic electroluminescent device of the present invention includes an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The electron transport region may also be formed using the compound of the present invention for a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL), although the material of the electron transport region may also be combined with one or more of ET-1 to ET-65 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer can adopt, but is not limited to, one or more compounds from ET-1 to ET-65 or one or more compounds from PH-1 to PH-46; mixtures of one or more compounds from ET-1 to ET-65 with one or more compounds from PH-1 to PH-46 may also be used, but are not limited thereto.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following:
LiQ、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca、Mg。
the specific reason why the above-mentioned compound of the present invention is excellent in performance is not clear, and it is presumed that the following reasons may be:
the compound provided by the invention takes an electron-deficient large conjugated structure of 5, 6-oxazoloquinoxaline as a parent nucleus and is connected with an Ar group, the compound structure has strong electron-deficient property and is favorable for electron injection, and meanwhile, the electron-deficient group of the large conjugated structure enables molecules to have good plane conjugation, thereby being favorable for improving the mobility of electrons. The aforementioned characteristics can enable molecules to show good electron injection and migration performance, so when the compound provided by the invention is used in an organic electroluminescent device, particularly as an electron transport material, the electron injection and migration efficiency in the device can be effectively improved, and the excellent effects of high luminous efficiency and low starting voltage of the device are ensured.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The synthetic route of the compound shown by the general formula of the invention is as follows:
(1) preparation of Compound (a)
In the first step of reaction, substituted 5-bromo-6-aminoquinoxaline and acyl chloride are refluxed in toluene solution containing triethylamine at 120 ℃ to obtain an amide intermediate M1 a; in the second step of reaction, the intermediate M1a is coupled and ring-closed under the catalysis of cuprous iodide to obtain the target compound (a) of 5, 6-oxazoloquinoxaline. Wherein R is1、R2、R3、R4L and Ar have the same meanings as in the general formula (1), Et3N is triethylamine, DMSO is dimethyl sulfoxide.
(2) Preparation of Compound (b)
In the first step of reaction, substituted 7-chloro-5-bromo-6-aminoquinoxaline and acyl chloride are refluxed in toluene solution containing triethylamine at 120 ℃ to obtain an amide intermediate M1 b; in the second step of reaction, coupling and ring closing the intermediate M1b under the catalysis of cuprous iodide to obtain an intermediate M2b of 5, 6-oxazoloquinoxaline; the third step is toAnd (3) coupling the intermediate M2b with aryl boronic acid Suzuki to obtain the target compound (b). Wherein R is1、R2、R3、R4L and Ar have the same meanings as in the general formula (1), Et3N is triethylamine, DMSO is dimethyl sulfoxide.
(3) Preparation of Compound (d)
In the first step of reaction, substituted 2-chloro-5-bromo-6-aminoquinoxaline and acyl chloride are refluxed in toluene solution containing triethylamine at 120 ℃ to obtain an amide intermediate M1 d; in the second step of reaction, coupling and ring closing the intermediate M1d under the catalysis of cuprous iodide to obtain an intermediate M2d of 5, 6-oxazoloquinoxaline; and thirdly, coupling the intermediate M2d with aryl boronic acid Suzuki to obtain the target compound (d). Wherein R is1、R2、R3、R4L and Ar have the same meanings as in the general formula (1), Et3N is triethylamine, DMSO is dimethyl sulfoxide.
Basic chemical materials such as ethanol, ethyl acetate, triethylamine, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, 1, 4-dioxane, dimethyl sulfoxide, potassium carbonate, potassium acetate, and cuprous iodide used in the synthesis method of the specific compound provided in the following synthesis examples were purchased from Shanghai Tantake technology Co., Ltd and Xiong chemical Co., Ltd. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
Synthesis example 1:
synthesis of Compound C1
(1) Preparation of Compound 1-1
The compound 2-bromo-3-amino-5-chloroquinoxaline (257g, 1.0mol) and triethylamine (202g, 2.0mol) were added to a 2L flask containing 1L of toluene, 4-chlorobenzoyl chloride (174g, 1.0mol) was slowly added dropwise with stirring at room temperature, and after completion of the addition, the reaction was refluxed with stirring at 120 ℃ for 8 hours, and TLC monitoring showed completion of the reaction. After cooling the reaction solution to room temperature, slowly pouring the reaction solution into 2L of water to precipitate a large amount of solid, and after suction filtration, carrying out column chromatography separation and purification on the solid to obtain the compound 1-1(332g, yield 84%).
(2) Preparation of Compounds 1-2
Compound 1-1(330g, 835mmol), anhydrous potassium carbonate (115g, 835mmol) and 1L of dimethyl sulfoxide were charged into a 2L flask, after replacing nitrogen, cuprous iodide (3.16g, 16.7mmol) was added, nitrogen was replaced 4 times, the reaction was refluxed at 110 ℃ for 10 hours with stirring, a large amount of solid was precipitated, and the end of the reaction was monitored by TLC. After the reaction is cooled to room temperature, the reaction liquid is filtered, the solid is leached with water and ethanol for three times respectively, the solid is dried, the filtrate is washed with saturated sodium bicarbonate solution and extracted with dichloromethane, organic phases are combined, and the solid and the organic phases are separated and purified by column chromatography to obtain the compound 1-2(247g, yield 94%).
(3) Preparation of Compounds 1-3
Compound 1-2(245g, 778mmol), phenylboronic acid (104g, 856mmol), and potassium acetate (215g, 1556mmol) were charged into a 5L flask containing 2L of tetrahydrofuran and 400mL of water, and after nitrogen gas was replaced with stirring at room temperature, [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (5.48g, 7.8mmol) was added, after nitrogen gas was replaced four times after completion of the addition, the mixture was refluxed for 6 hours with stirring to precipitate a large amount of solid, and the end of the reaction was monitored by TLC. Tetrahydrofuran and water were removed by rotary evaporation, the solid was washed with water and ethanol, respectively, dried and purified by column chromatography to give compound 1-3(244g, 88% yield).
(4) Preparation of Compounds 1-4
Compound 1-3(242g, 678mmol), pinacol diboron ester (258g, 1017mmol), and potassium acetate (187g, 1356mmol) were charged into a 5L flask containing 3L of 1, 4-dioxane, and after nitrogen exchange at room temperature with stirring, palladium acetate (3.1g, 13.6mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (11.2g, 27.2mmol) were added. After the addition was completed, nitrogen was replaced four times, the reaction was refluxed with stirring for 4 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, the mixture was separated with water and dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compounds 1 to 4(253g, yield 83%).
(5) Preparation of Compound C1
Compounds 1-4(10g, 22.3mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (5.9g, 22.3mmol), potassium carbonate (6.2g, 44.6mmol), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (146mg, 0.2mmol) were added to a flask containing 100mL tetrahydrofuran and 25mL water, the nitrogen was replaced and the reaction was heated to reflux under nitrogen for 4 hours, TLC indicated complete reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to obtain compound C1(10.5g, yield 85%). Calculated molecular weight: 554.19, found C/Z: 554.2.
synthesis example 2:
synthesis of Compound C3
(1) Preparation of Compound 2-1
Adding 50g (256mmol, 1.0eq) of 2, 4-dichloroquinazoline into a 1L single-neck bottle, adding 400mL of dichloromethane, cooling to 0 ℃ in an ice bath, adding 64g (632mmol, 3.0eq) of triethylamine, stirring until a reaction solution is clear, dropwise adding 18.6g (316mmol, 1.5eq) of hydrazine hydrate in the ice bath, gradually precipitating solids in the reaction process, stirring for 3 hours, monitoring the reaction by TLC, allowing the raw materials to disappear, adding 4.0L of water, and continuing stirring for 1 hour. Filtration and drying were carried out to obtain Compound 2-1(41.2g, yield: 83%).
(2) Preparation of Compound 2-2
40g of Compound 2-1(206mmol, 1.0eq), 19.8g of benzaldehyde (227mmol, 1.1eq) and 500mL of ethanol were added to a 1.0L single-neck flask, and stirring was continued for 30 minutes after the solution was clear, and disappearance of the starting material was monitored by TLC. 73g (227mmol, 1.1eq) iodobenzene diacetic acid was added portionwise (temperature controlled below 20 ℃ C. for the addition). After the addition was completed, stirring was carried out overnight, a solid was gradually precipitated, TLC monitored reaction was completed, filtration was carried out, the filter cake was rinsed with ethanol until the filtrate was colorless clear liquid, rinsed with Petroleum Ether (PE) for 2 to 3 times, and dried to obtain compound 2-2(46g, yield: 81%).
(3) Preparation of Compound C3
Compound 2-2(10g, 35.7mmol), compound 1-4(16g, 35.7mmol), potassium carbonate (9.9g, 71.4mmol), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (263mg, 0.36mmol) was added to a flask containing 160mL of tetrahydrofuran and 40mL of water, the nitrogen was replaced and the reaction was heated under reflux under nitrogen for 4 hours, TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C3(17.6g, yield 87%). Calculated molecular weight: 567.18, found C/Z: 567.2.
synthesis example 3:
synthesis of Compound C17
Compound 1-4(10g, 22.3mmol), 9-bromo-10- (1-naphthyl) anthracene (8.5g, 22.3mmol), potassium carbonate (6.2g, 44.6mmol), tetrakistriphenylphosphine palladium (0.25g, 0.22mmol) were added to a flask containing 100mL of toluene, 20mL of ethanol, and 20mL of water, the reaction was refluxed for 6 hours under nitrogen atmosphere with replacement of nitrogen, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C17(11.3g, yield 81%). Calculated molecular weight: 625.22, found C/Z: 625.2.
synthesis example 4:
synthesis of Compound C22
(1) Preparation of Compound 4-1
The compound 2, 4-dibromo-3-amino-5-chloroquinoxaline (33.5g, 100mmol) and triethylamine (20.2g, 200mmol) were added to a 1L flask containing 200mL of toluene, 4-chlorobenzoyl chloride (17.4g, 100mmol) was slowly added dropwise with stirring at room temperature, and after completion of addition, the reaction was stirred at 120 ℃ for reflux reaction for 6 hours, and TLC monitoring showed completion of the reaction. After the reaction solution was cooled to room temperature, it was slowly poured into 1L of water to precipitate a large amount of solid, which was then filtered off with suction and purified by column chromatography to obtain compound 4-1(40.7g, yield 86%).
(2) Preparation of Compound 4-2
Compound 4-1(40g, 84.5mmol), anhydrous potassium carbonate (12g, 84.5mmol) and 200mL of dimethyl sulfoxide were charged into a 1L flask, after replacing nitrogen, cuprous iodide (0.32g, 1.7mmol) was added, replacing nitrogen 4 times, the reaction was refluxed for 8 hours at 110 ℃ with stirring, and a large amount of solid precipitated, and the end of the reaction was monitored by TLC. After the reaction is cooled to room temperature, the reaction liquid is filtered, the solid is leached with water and ethanol for three times respectively, the solid is dried, the filtrate is washed with saturated sodium bicarbonate solution and extracted with dichloromethane, organic phases are combined, and the solid and the organic phases are separated and purified by column chromatography to obtain the compound 4-2(25.9g, the yield is 78%).
(3) Preparation of Compound 4-3
Compound 4-2(25g, 63.6mmol), phenylboronic acid (8.5g, 70mmol), potassium carbonate (17.6g, 127.2mmol), tetrakistriphenylphosphine palladium (0.74g, 0.64mmol) were added to a flask containing 200mL of toluene, 40mL of ethanol, and 40mL of water, the reaction was refluxed under nitrogen atmosphere for 4 hours, and TLC showed completion of the reaction. The precipitated solid is filtered, rinsed with water and ethanol respectively, dried and purified by column chromatography to obtain the compound 4-3(21.2g, yield 80%).
(4) Preparation of Compound 4-4
Compound 4-3(21g, 50.5mmol), phenylboronic acid (6.7g, 55.5mmol), potassium carbonate (13.9g, 101mmol), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (366mg, 0.5mmol) was added to a 1L flask containing 200mL of tetrahydrofuran and 50mL of water, the nitrogen was replaced and the reaction was heated under reflux under nitrogen for 5 hours, TLC indicated completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound 4-4(19.4g, yield 84%).
(5) Preparation of Compounds 4-5
Compound 4-4(19g, 41.5mmol), pinacol diboron (15.8g, 62.3mmol) and potassium acetate (8.1g, 83mmol) were charged into a 1L flask containing 300mL of 1, 4-dioxane, and after replacing nitrogen with palladium acetate (187mg, 0.83mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.68g, 1.66mmol) were added under stirring at room temperature. After the addition was completed, nitrogen was replaced four times, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, the mixture was separated with water and dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 4-5(17.8g, yield 78%).
(6) Preparation of Compound C22
Compound 4-5(17g, 31mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (8.2g, 31mmol), potassium carbonate (8.6g, 62mmol), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (219mg, 0.3mmol) was added to a flask containing 200mL of tetrahydrofuran and 50mL of water, the nitrogen was replaced and the reaction was refluxed under nitrogen for 6 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C22(15.6g, yield 77%). Calculated molecular weight: 655.21, found C/Z: 655.2.
synthesis example 5:
synthesis of Compound C30
Compound 1-4(10g, 22.3mmol), 2-bromo-9, 9-spirobifluorene (8.8g, 22.3mmol), potassium carbonate (6.2g, 44.6mmol), tetrakistriphenylphosphine palladium (0.25g, 0.22mmol) were added to a flask containing 100mL of toluene, 20mL of ethanol, and 20mL of water, the nitrogen was replaced and the reaction was refluxed under nitrogen for 6 hours, TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C30(11.9g, yield 84%). Calculated molecular weight: 637.22, found C/Z: 637.2.
synthesis example 6:
synthesis of Compound C41
(1) Preparation of Compound 6-1
The compound 2-bromo-3-amino-5-chloroquinoxaline (25.7g, 100mmol) and triethylamine (20.2g, 200mmol) were added to a 1L flask containing 200mL of toluene, benzoyl chloride (14g, 100mmol) was slowly added dropwise with stirring at room temperature, and after the addition, the reaction was stirred at 120 ℃ for 4 hours under reflux, and TLC monitoring showed completion of the reaction. After the reaction solution was cooled to room temperature, it was slowly poured into 1L of water to precipitate a large amount of solid, which was then filtered off with suction and purified by column chromatography to obtain compound 6-1(31.4g, yield 87%).
(2) Preparation of Compound 6-2
Compound 6-1(31g, 86mmol), anhydrous potassium carbonate (23.7g, 172mmol) and 200mL of dimethyl sulfoxide were charged into a 1L flask, after replacing nitrogen, cuprous iodide (0.32g, 1.7mmol) was added, and after replacing nitrogen, the reaction was refluxed for 6 hours under stirring at 110 ℃ for 4 times, and a large amount of solid precipitated, and the end of the reaction was monitored by TLC. After the reaction is cooled to room temperature, the reaction solution is filtered, the solid is rinsed with water and ethanol for three times respectively, the solid is dried, the filtrate is washed with saturated sodium bicarbonate solution and extracted with dichloromethane, organic phases are combined, and the solid and the organic phases are separated and purified by column chromatography to obtain the compound 6-2(22.2g, the yield is 92%).
(3) Preparation of Compound C41
Compound 6-2(10g, 35.6mmol), 2, 4-diphenyl-6- (4-pinacolboronate) phenyl-1, 3, 5-triazine (17g, 39.1mmol), potassium carbonate (9.8g, 71.2mmol), tris-dibenzylideneacetone dipalladium (0.65g, 0.71mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.57g, 1.4mmol) were charged into a 1L flask containing 200mL of 1, 4-dioxane and 20mL of water, the nitrogen was replaced and the reaction was refluxed under nitrogen atmosphere for 4 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C41(15.2g, yield 77%). Calculated molecular weight: 554.19, found C/Z: 554.2.
synthesis example 7:
synthesis of Compound C59
(1) Preparation of Compound 7-1
Compound 6-2(10g, 35.6mmol), 3-chlorobenzeneboronic acid (6.1g, 39.2mmol), potassium carbonate (9.8g, 71.2mmol), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (263mg, 0.36mmol) was added to a flask containing 100mL of tetrahydrofuran and 25mL of water, the nitrogen was replaced and the reaction was heated under reflux under nitrogen for 4 hours, TLC indicated completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound 7-1(10.5g, yield 83%).
(2) Preparation of Compound C59
Compound 7-1(10g, 28mmol), 2, 4-diphenyl-6- (3-pinacolboronato) phenyl-1, 3, 5-triazine (12.2g, 28mmol), potassium carbonate (7.7g, 56mmol), tris-dibenzylideneacetone dipalladium (0.51g, 0.56mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.46g, 1.12mmol) were added to a 1L flask containing 200mL of 1, 4-dioxane and 20mL of water, the reaction was refluxed for 6 hours under nitrogen with nitrogen replaced, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to obtain compound C59(13.1g, yield 74%). Calculated molecular weight: 630.22, found C/Z: 630.2.
comparative Synthesis example 1
Synthesis of comparative compound D1:
the compound 2-bromo-1H-imidazole- [4,5-f ] quinoxaline (10g, 40.3mmol), N-phenylcarbazole-3-boronic acid (11.6g, 40.3mmol), potassium carbonate (11.1g, 80.6mmol), tetrakistriphenylphosphine palladium (0.46g, 0.4mmol) was added to a flask containing 100mL of toluene, 20mL of ethanol, and 20mL of water, the nitrogen was replaced and the reaction was refluxed under nitrogen atmosphere for 6 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound D1(14.6g, yield 88%). Calculated molecular weight: 411.15, found C/Z: 411.2.
device example 1
The embodiment provides a preparation method of an organic electroluminescent device, which comprises the following specific steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing until the pressure is less than 10-5Pa, performing vacuum evaporation on the anode layer film to obtain HI-3 serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-4 on the hole injection layer in vacuum to serve as a first hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 40 nm;
evaporating HT-14 on the first hole transport layer in vacuum to serve as a second hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 10 nm;
a luminescent layer of the device is vacuum evaporated on the second hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material BFH-4 is adjusted to be 0.1nm/s, the evaporation rate of the dye BFD-6 is set in a proportion of 5%, and the total film thickness of evaporation is 20nm by using a multi-source co-evaporation method;
vacuum evaporating ET-17 on the luminescent layer to be used as a hole blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 5 nm;
evaporating the compounds C1 and ET-57 of the invention on the hole blocking layer by a multi-source co-evaporation method to be used as an electron transport layer, adjusting the evaporation rate of the compound C1 to be 0.1nm/s, setting the ratio of the evaporation rate of the compound C1 to the evaporation rate of the ET-57 to be 100% (the ratio of the evaporation rates of C1 and ET-57 is 1:1), and setting the total thickness of the evaporated film to be 23 nm;
LiF with the thickness of 1nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 80nm is used as a cathode of the device.
Device examples 2 to 7 differ from device example 1 only in that the compound C1 according to the invention used in the electron transport layer was replaced by another compound according to the invention, as specified in table 1.
Comparative device example 1
The difference from device example 1 is that the compound C1 according to the invention used in the electron transport layer was replaced by the prior art compound D1.
And (3) performance testing:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples and comparative examples were measured at the same brightness using a PR 750 type photoradiometer of Photo Research, a ST-86LA type brightness meter (photoelectric instrument factory of university of beijing) and a Keithley4200 test system. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency;
the results of the performance tests are shown in table 1.
Table 1:
as can be seen from table 1, in the case that the material schemes and the preparation processes of other functional layers in the organic electroluminescent device structure are completely the same, compared with the comparative example, the organic electroluminescent devices provided in the device examples 1 to 7 of the present invention have higher current efficiency and lower driving voltage, and in the device examples 1 to 7, the current efficiency of the device is 6.84 to 7.33cd/a, and the driving voltage of the device is 3.76 to 4.21V.
The parent nucleus of the compound is an electron-deficient large conjugated structure of 5, 6-oxazoloquinoxaline, Ar is connected with the parent nucleus, so that the whole compound has higher electron injection and migration performance, a device has higher current efficiency and lower driving voltage, and the technical effect of the invention cannot be realized by replacing the parent nucleus with other structures (such as a comparative compound D1 in the prior art).
The experimental data show that the novel organic material is an organic luminescent functional material with good performance as an electron transport material of an organic electroluminescent device, and has wide application prospect.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (8)
1. A compound of the general formula (I) has a structure represented by formula (1);
in the formula (1), X is S or O;
in formula (1), the R represents one substituent to the maximum permissible substituent, and is independently selected from hydrogen, deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, and when the number of R is multiple, adjacent R can be connected in a condensed mode;
in the formula (1), L is selected from one of single bond, substituted or unsubstituted arylene of C6-C60 and substituted or unsubstituted heteroarylene of C3-C60;
in the formula (1), Ar is selected from one of substituted or unsubstituted aryl of C6-C60 and substituted or unsubstituted heteroaryl of C3-C60;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
2. The compound according to claim 1, which has any one of the following structures represented by formulae (1-1) to (1-3):
in the formulae (1-1) to (1-3), the X, R, Ar and L are defined as in the formula (1).
3. The compound according to claim 1, having any one of the following structures represented by formulae (a) to (j):
in the formulae (a) to (j), R1-R4The same or different, and each is independently selected from one of hydrogen, deuterium, halogen, cyano, nitro, alkenyl, alkynyl, carboxyl, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, and R is1-R4Wherein two adjacent groups may be connected by fusion;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
4. A compound according to any one of claims 1 to 3, wherein Ar is selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, cyano;
the Ar is preferably substituted or unsubstituted C3-C30 electron deficient heteroaryl or cyano.
5. A compound according to any one of claims 1 to 3, wherein Ar is selected from cyano or from any one of the following substituted or unsubstituted groups:
wherein, the wavy line
Represents a linking site;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
6. The compound of claim 1, having the structure shown below:
7. use of a compound according to any one of claims 1 to 6 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or electronic paper;
preferably, the compound is used as an electron transport material in an organic electroluminescent device.
8. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the compound according to any one of claims 1 to 6;
preferably, the light-emitting functional layer comprises a hole transport region, a light-emitting layer and an electron transport region, the hole transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is arranged between the hole transport region and the electron transport region; wherein the electron transport region comprises an electron transport layer containing the compound of any one of claims 1 to 6.
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| CN115073440A (en) * | 2022-07-21 | 2022-09-20 | 长春海谱润斯科技股份有限公司 | Compound with benzoxazole ring and organic electroluminescent device thereof |
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| CN105272978A (en) * | 2014-05-26 | 2016-01-27 | 中国医学科学院药物研究所 | Quinoxalinone compound, preparation method and anti-hepatitis C virus use thereof |
| CN115175973A (en) * | 2020-03-12 | 2022-10-11 | 株式会社P&H Tech | Organic light emitting compound and organic light emitting device including the same |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4977155A (en) * | 1988-06-28 | 1990-12-11 | A/S Ferrosan | 1,2,3-triazolo compounds |
| CN105272978A (en) * | 2014-05-26 | 2016-01-27 | 中国医学科学院药物研究所 | Quinoxalinone compound, preparation method and anti-hepatitis C virus use thereof |
| CN115175973A (en) * | 2020-03-12 | 2022-10-11 | 株式会社P&H Tech | Organic light emitting compound and organic light emitting device including the same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115073440A (en) * | 2022-07-21 | 2022-09-20 | 长春海谱润斯科技股份有限公司 | Compound with benzoxazole ring and organic electroluminescent device thereof |
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